A look at the player who failed at Spurs, Manchester United and other teams besides - but could now get a second chance.
Few footballers go from playing with Real Madrid to being a first-team regular at Tottenham Hotspur to being a discarded free agent by the age of 28, unless they’ve had some trouble with injuries – but that’s precisely the situation that a seemingly fit and healthy Sergio Reguilón finds himself in now.
Having made just six appearances and two starts for Spurs over the 2024/25 season, the Spaniard’s contract is finally up and he is free to seek a new club, with both West Ham United and Everton have been widely linked. But having played so little for so long, is Reguilón still a player worth having in a Premier League squad? And just why did it all go so wrong at Spurs?
Why Sergio Reguilón’s career went south at Spurs
When Reguilón first joined Spurs, he hit the ground running at some speed and was a cast-iron regular under José Mourinho – and played so well that many Spurs fans were concerned that Real Madrid might be tempted to activate a £40m buy-back clause in the deal that took him to North London. Under Mourinho’s successor, however, his playing style saw him fall down the pecking order.
An instinctively attacking wing-back who was at his most dangerous on the overlap, his relative lack of ability to progress the ball in possession cost him credit under Antonio Conte, and a groin injury which he struggled to shake off saw him go from an indispensable starter to an afterthought.
Loan spells followed in their droves. He spent some time at Atlético Madrid but couldn’t make it stick. Then Manchester United drafted him in as injury cover only to terminate his temporary deal when Luke Shaw returned – however temporarily – from one of his many lay-offs.
Six months at Brentford followed, but they were never realistically able to afford to cover his reported £100,000 per week wages and a permanent move wasn’t on the table. Reguilón had hoped to fight his way back into Ange Postecoglou’s thoughts last summer but, having received encouragement from his recently-fired boss, found himself on the outside once more.
“I didn’t understand and still don’t understand the situation,” Reguilón told The Times. “During pre-season I was very happy and Postecoglou was happy with me, also the staff. I was playing like a normal player, all the games… The next day I was out of the training and I didn’t know what happened… I don’t think it’s performance reason, I think it’s another reason. This is football, this is business”.
Business to an extent, perhaps, especially given that his first-team place had long since been taken up by Destiny Udogie and Spurs wanted to find a buyer in the transfer market, but the Spaniard was also a victim of his own style of football.
A natural in the world of the overlapping wing-back, he struggled to adapt to a new reality in which full-backs often played a more supporting role, coming into the middle of the pitch and supporting the build-up from narrower areas. Reguilón, a fine crosser of the ball but a sub-par passer who didn’t offer stability or control in such positions, became somewhat old-fashioned.
So it is that Postecoglou, who only occasionally allowed Udogie to bomb on to the byline, couldn’t find room for Reguilón in his side and he was used only in emergencies and was not registered for the Europa League squad, although he was given a winner’s medal regardless. And now he finds himself out of work entirely, and looking for a team whose playing style suits his own – and to prove that he’s still a force to be reckoned with.
Why West Ham & Everton could benefit from giving Reguilón a second chance
While few teams in the Premier League still use the kind of highly-aggressive overlapping wing-backs that were de rigeur through most of the 2010s, two of those that do – West Ham and Everton – are among the clubs said to be considering a move for Reguilón, with Caught Offside claiming that both they and Bournemouth are among the suitors.
Everton, for their part, made an £18m bid for Reguilón back in 2020 before he moved to Spurs, and could end a long wait to sign a player they have admired for some time. Under David Moyes, they still look to get their full-backs forward into crossing positions and still play with the kind of relatively direct football which plays to the Spaniard’s strengths and mitigates his technical weaknesses.
West Ham, under Graham Potter, also use wing-backs higher upfield, albeit in a rather different way – since taking over at the London Stadium, Potter has often operated with a 3-4-2-1 formation which allowed the wing-backs to get around and ahead of attacking players such as Jarrod Bowen and the departed Mohammed Kudus.
Technically, Potter’s pass-focussed methodology may not entirely suit Reguilón, a player whose pass completion rate over the last two seasons has been below 70%, very low for a modern full-back of any kind – but he also emphasises the use of his wide defenders in the attacking phase, as evinced by the use of Aaron Wan-Bissaka, who put in 76 crosses in the Premier League in 2024/25, more than he had in the previous three campaigns combined.
Wan-Bissaka’s stylistic transmogrification began, of course, under Moyes, and the consistent improvement in the former Manchester United defender’s attacking production hints at the way both Everton and West Ham could potentially get the best out of a player who has proven his ability to play at the top level, even if he has been on the fringes for three long years now.
Bournemouth, too, are direct in their attacking methods and need a wing-back who can get forward and wide to replace Milos Kerkez, who has left for Liverpool. While the rumour mill often throws up false connections and baseless speculation, there is an undeniable tactical logic behind the notion of any of these teams making a deal for Reguilón.
His wage demands will be a factor, of course, but the fact that he can be signed without a transfer fee will make him an appealing player to take a chance on. Under the right circumstances, Reguilón could well thrive once more.
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